Sodium Methoxide → (E)-methyl 3-(4-((2-(4-isopropyloxazol-5-yl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632665Notes

Reaction equation

[CH:1]([C:3]1[S:7][C:6]2[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:5]=2[C:4]=1[O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1)=[O:2].[N+:27]([CH:29](S(C1C=CC(C)=CC=1)(=O)=O)[CH:30]([CH3:32])[CH3:31])#[C-:28].C[O-].[Na+]>CO>[CH:30]([C:29]1[N:27]=[CH:28][O:2][C:1]=1[C:3]1[S:7][C:6]2[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:5]=2[C:4]=1[O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1)([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (E)-methyl 3-(4-((2-formyl-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (30 mg, 0.081 mmol) and 1-((l-isocyano-2-methylpropyl)sulfonyl)-4-methylbenzene (38.7 mg, 0.163 mmol) in MeOH (1.5 mL) at room temperature was added NaOMe (13.20 mg, 0.244 mmol) as a solid. The resulting mixture was warmed to 80° C. for 3 h after which time the reaction was quenched by addition of brine and extracted with EtOAc (2×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography (SiO2, 0-20% EtOAc/Heptane) to afford (E)-methyl 3-(4-((2-(4-isopropyloxazol-5-yl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (10 mg, 0.022 mmol, 27% yield) as a yellow oil. LC/MS (m/z, MH+): 450.0.

Workup

customwas quenched by addition of brine
extractionextracted with EtOAc (2×)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting crude material was purified by column chromatography (SiO2, 0-20% EtOAc/Heptane)

Sources & evidence

ORD record: ord-cd3e6e9123114bf6b55a421baa9f6b13
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321746B2

Reaction notes

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